CA2300273A1 - Derives d'amine et leur methode de production - Google Patents
Derives d'amine et leur methode de production Download PDFInfo
- Publication number
- CA2300273A1 CA2300273A1 CA002300273A CA2300273A CA2300273A1 CA 2300273 A1 CA2300273 A1 CA 2300273A1 CA 002300273 A CA002300273 A CA 002300273A CA 2300273 A CA2300273 A CA 2300273A CA 2300273 A1 CA2300273 A1 CA 2300273A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- group
- tert
- methyl
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 150000001412 amines Chemical class 0.000 title claims abstract description 224
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- -1 4-(1-methyl-1-phenylethyl)benzyl Chemical group 0.000 claims abstract description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 1000
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 198
- 239000000203 mixture Substances 0.000 claims description 65
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 63
- 125000004122 cyclic group Chemical group 0.000 claims description 56
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 44
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 17
- 230000001857 anti-mycotic effect Effects 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000002543 antimycotic Substances 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000003429 antifungal agent Substances 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- UQFFJQUINHEOME-SOFGYWHQSA-N (e)-n-[2-(3,4-difluorophenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(F)C(F)=C1 UQFFJQUINHEOME-SOFGYWHQSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- YTRBFANAYGWRCT-UXBLZVDNSA-N (e)-n,6,6-trimethyl-n-[2-(2-nitrophenyl)prop-2-enyl]hept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=CC=C1[N+]([O-])=O YTRBFANAYGWRCT-UXBLZVDNSA-N 0.000 claims description 7
- WCKCRTGGXQKMJF-CSKARUKUSA-N (e)-n-[2-(3,4-dimethylphenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(C)C(C)=C1 WCKCRTGGXQKMJF-CSKARUKUSA-N 0.000 claims description 7
- ZWDFODUMPHVFGX-SOFGYWHQSA-N (e)-n-[2-(3-bromophenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=CC(Br)=C1 ZWDFODUMPHVFGX-SOFGYWHQSA-N 0.000 claims description 7
- WKKRHBBDRALMIW-KQEMPYGNSA-N CC(C#CC=CCN(C)C/C=C/C1=CC=C(C#N)C=C1)(C)C Chemical compound CC(C#CC=CCN(C)C/C=C/C1=CC=C(C#N)C=C1)(C)C WKKRHBBDRALMIW-KQEMPYGNSA-N 0.000 claims description 7
- LRIYYRXHLGLRPM-BGVPZGPGSA-N CC(C)(C)C#CC=CCN(C)C\C=C\C1=CC=CC(C#N)=C1 Chemical compound CC(C)(C)C#CC=CCN(C)C\C=C\C1=CC=CC(C#N)=C1 LRIYYRXHLGLRPM-BGVPZGPGSA-N 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- WFYYPRSNOUXIML-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-phenyl-n-propan-2-ylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C(C)C)CC(=C)C1=CC=CC=C1 WFYYPRSNOUXIML-UHFFFAOYSA-N 0.000 claims description 7
- FPONCXWUCOKTJS-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-(2-nitrophenyl)prop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=CC=C1[N+]([O-])=O FPONCXWUCOKTJS-UHFFFAOYSA-N 0.000 claims description 7
- IGZZGFXZDGTICF-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-(4-nitrophenyl)prop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C([N+]([O-])=O)C=C1 IGZZGFXZDGTICF-UHFFFAOYSA-N 0.000 claims description 7
- LZRGIFUCJQVQOT-UHFFFAOYSA-N n-methyl-n-(naphthalen-2-ylmethyl)-2-phenylprop-2-en-1-amine Chemical compound C=1C=C2C=CC=CC2=CC=1CN(C)CC(=C)C1=CC=CC=C1 LZRGIFUCJQVQOT-UHFFFAOYSA-N 0.000 claims description 7
- UNBBPNCXXWGZHX-VQHVLOKHSA-N (e)-n,6,6-trimethyl-n-[2-(3-methylphenyl)prop-2-enyl]hept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=CC(C)=C1 UNBBPNCXXWGZHX-VQHVLOKHSA-N 0.000 claims description 6
- QRLFRADJUUVJDW-VQHVLOKHSA-N (e)-n,6,6-trimethyl-n-[2-(4-methylphenyl)prop-2-enyl]hept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(C)C=C1 QRLFRADJUUVJDW-VQHVLOKHSA-N 0.000 claims description 6
- JETPBFNVIOUKEG-SOFGYWHQSA-N (e)-n,6,6-trimethyl-n-[2-(4-nitrophenyl)prop-2-enyl]hept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C([N+]([O-])=O)C=C1 JETPBFNVIOUKEG-SOFGYWHQSA-N 0.000 claims description 6
- NVACAEGQJUUXEF-CSKARUKUSA-N (e)-n-[2-(2,4-dimethylphenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(C)C=C1C NVACAEGQJUUXEF-CSKARUKUSA-N 0.000 claims description 6
- OFULRFIPAVRRDK-YRNVUSSQSA-N (e)-n-[2-(2-methoxyphenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound COC1=CC=CC=C1C(=C)CN(C)C\C=C\C#CC(C)(C)C OFULRFIPAVRRDK-YRNVUSSQSA-N 0.000 claims description 6
- PQBZEDPFJSBDNJ-SOFGYWHQSA-N (e)-n-[2-(4-bromophenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(Br)C=C1 PQBZEDPFJSBDNJ-SOFGYWHQSA-N 0.000 claims description 6
- ODRGXZWJHJUBTF-UHFFFAOYSA-N 1-(3-bromophenyl)-2-[(4-tert-butylphenyl)methyl-methylamino]ethanone Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=O)C1=CC=CC(Br)=C1 ODRGXZWJHJUBTF-UHFFFAOYSA-N 0.000 claims description 6
- RVEBEGZWZIRDNA-UHFFFAOYSA-N 1-(4-bromophenyl)-2-[(4-tert-butylphenyl)methyl-methylamino]ethanone Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=O)C1=CC=C(Br)C=C1 RVEBEGZWZIRDNA-UHFFFAOYSA-N 0.000 claims description 6
- IJNZFMZUIURHKH-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2-[methyl(naphthalen-1-ylmethyl)amino]ethanone Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)CC(=O)C1=CC=C(C(C)(C)C)C=C1 IJNZFMZUIURHKH-UHFFFAOYSA-N 0.000 claims description 6
- DSNSWGHRPPTVNE-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-n-[(4-tert-butylphenyl)methyl]-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C(C(C)(C)C)C=C1 DSNSWGHRPPTVNE-UHFFFAOYSA-N 0.000 claims description 6
- OFUPRRQHMDLDSF-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-n-methyl-n-(naphthalen-1-ylmethyl)prop-2-en-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)CC(=C)C1=CC=C(C(C)(C)C)C=C1 OFUPRRQHMDLDSF-UHFFFAOYSA-N 0.000 claims description 6
- MCYJHJMQVFVRAO-WEVVVXLNSA-N 2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]-1-(2-hydroxyphenyl)ethanone Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC=CC=C1O MCYJHJMQVFVRAO-WEVVVXLNSA-N 0.000 claims description 6
- VUFBZGLOVKNSAL-UHFFFAOYSA-N 4-[3-[(4-tert-butylphenyl)methyl-methylamino]prop-1-enyl]benzonitrile Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC=CC1=CC=C(C#N)C=C1 VUFBZGLOVKNSAL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- VDTXDAKIQHJXNO-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-(3-methylphenyl)prop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=CC(C)=C1 VDTXDAKIQHJXNO-UHFFFAOYSA-N 0.000 claims description 6
- MXETVQURCXOKPQ-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-naphthalen-2-ylprop-2-en-1-amine Chemical compound C=1C=C2C=CC=CC2=CC=1C(=C)CN(C)CC1=CC=C(C(C)(C)C)C=C1 MXETVQURCXOKPQ-UHFFFAOYSA-N 0.000 claims description 6
- DFMURVUCVBNNSI-UHFFFAOYSA-N n-methyl-n-(naphthalen-1-ylmethyl)-2-phenylprop-2-en-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)CC(=C)C1=CC=CC=C1 DFMURVUCVBNNSI-UHFFFAOYSA-N 0.000 claims description 6
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 5
- UBBULJBPQQHZQW-SOFGYWHQSA-N (e)-n,6,6-trimethyl-n-[2-(3-nitrophenyl)prop-2-enyl]hept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=CC([N+]([O-])=O)=C1 UBBULJBPQQHZQW-SOFGYWHQSA-N 0.000 claims description 5
- VTHOUDOZJACZBJ-UXBLZVDNSA-N (e)-n-[2-(2-fluorophenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=CC=C1F VTHOUDOZJACZBJ-UXBLZVDNSA-N 0.000 claims description 5
- KIAHNDYSCPMLTL-PKNBQFBNSA-N (e)-n-[2-(4-tert-butylphenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(C(C)(C)C)C=C1 KIAHNDYSCPMLTL-PKNBQFBNSA-N 0.000 claims description 5
- CCHNKKCRZUYBGN-ACCUITESSA-N (e)-n-[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 CCHNKKCRZUYBGN-ACCUITESSA-N 0.000 claims description 5
- BCMIRKCBYCHRGC-UHFFFAOYSA-N 1-(2-bromophenyl)-2-[(4-tert-butylphenyl)methyl-methylamino]ethanone Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=O)C1=CC=CC=C1Br BCMIRKCBYCHRGC-UHFFFAOYSA-N 0.000 claims description 5
- SRBPOKWONWEZGQ-WEVVVXLNSA-N 1-(2-bromophenyl)-2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]ethanone Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC=CC=C1Br SRBPOKWONWEZGQ-WEVVVXLNSA-N 0.000 claims description 5
- DWKCMMDHCMCISI-FNORWQNLSA-N 1-(3,5-difluorophenyl)-2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]ethanone Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC(F)=CC(F)=C1 DWKCMMDHCMCISI-FNORWQNLSA-N 0.000 claims description 5
- ARMAKIKNCOYZBB-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2-[(4-tert-butylphenyl)methyl-methylamino]ethanone Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=O)C1=CC=C(C(C)(C)C)C=C1 ARMAKIKNCOYZBB-UHFFFAOYSA-N 0.000 claims description 5
- WZNJSUBQWMASTB-UHFFFAOYSA-N 2-[(4-tert-butylphenyl)methyl-methylamino]-1-naphthalen-2-ylethanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)CN(C)CC1=CC=C(C(C)(C)C)C=C1 WZNJSUBQWMASTB-UHFFFAOYSA-N 0.000 claims description 5
- MTWCVUCNRRFTMA-UHFFFAOYSA-N 2-[3-[(4-tert-butylphenyl)methyl-methylamino]prop-1-en-2-yl]aniline Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=CC=C1N MTWCVUCNRRFTMA-UHFFFAOYSA-N 0.000 claims description 5
- CXZXTJKRARQPRJ-UXBLZVDNSA-N 2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]-1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(=O)CN(C)C\C=C\C#CC(C)(C)C CXZXTJKRARQPRJ-UXBLZVDNSA-N 0.000 claims description 5
- UAMYKPZOZWHAHG-SOFGYWHQSA-N 2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]-1-(3-methylphenyl)ethanone Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC=CC(C)=C1 UAMYKPZOZWHAHG-SOFGYWHQSA-N 0.000 claims description 5
- PJAMPTVFGSTSKQ-FNORWQNLSA-N 3-[2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]acetyl]benzonitrile Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC=CC(C#N)=C1 PJAMPTVFGSTSKQ-FNORWQNLSA-N 0.000 claims description 5
- CEJJCAOZYFQCTQ-UHFFFAOYSA-N ethyl 4-[3-[(4-tert-butylphenyl)methyl-methylamino]prop-1-enyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C=CCN(C)CC1=CC=C(C(C)(C)C)C=C1 CEJJCAOZYFQCTQ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- UZTPVVJWVYXALI-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(2,4-dichlorophenyl)-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C(Cl)C=C1Cl UZTPVVJWVYXALI-UHFFFAOYSA-N 0.000 claims description 5
- CAUAPGBKPGYWKZ-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(2,4-dimethylphenyl)-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C(C)C=C1C CAUAPGBKPGYWKZ-UHFFFAOYSA-N 0.000 claims description 5
- XWPXJQAATUAERZ-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(3,4-dichlorophenyl)-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C(Cl)C(Cl)=C1 XWPXJQAATUAERZ-UHFFFAOYSA-N 0.000 claims description 5
- ABWUTHMCDXWDGP-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(3,4-difluorophenyl)-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C(F)C(F)=C1 ABWUTHMCDXWDGP-UHFFFAOYSA-N 0.000 claims description 5
- VAXNMEAWABARRE-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(3-fluorophenyl)-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=CC(F)=C1 VAXNMEAWABARRE-UHFFFAOYSA-N 0.000 claims description 5
- AOEUMTLLWJKCMZ-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-2-(3-methoxyphenyl)-n-methylprop-2-en-1-amine Chemical compound COC1=CC=CC(C(=C)CN(C)CC=2C=CC(=CC=2)C(C)(C)C)=C1 AOEUMTLLWJKCMZ-UHFFFAOYSA-N 0.000 claims description 5
- XHTAXAJYDPJECE-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n,3-dimethyl-2-phenylbut-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C(C)C)C1=CC=CC=C1 XHTAXAJYDPJECE-UHFFFAOYSA-N 0.000 claims description 5
- NMHRAUQJSQXRCB-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-(2-methylphenyl)prop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=CC=C1C NMHRAUQJSQXRCB-UHFFFAOYSA-N 0.000 claims description 5
- ARXGTVBRQIFHDR-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-phenylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=CC=C1 ARXGTVBRQIFHDR-UHFFFAOYSA-N 0.000 claims description 5
- SPBINJKZTKLSPH-FNORWQNLSA-N 1-(2,4-dichlorophenyl)-2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]ethanone Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC=C(Cl)C=C1Cl SPBINJKZTKLSPH-FNORWQNLSA-N 0.000 claims description 4
- XOHRUYDSBQYBAS-UHFFFAOYSA-N 2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-n-[(4-tert-butylphenyl)methyl]-n-methylprop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 XOHRUYDSBQYBAS-UHFFFAOYSA-N 0.000 claims description 4
- UGOLIEHVMIQBSZ-SOFGYWHQSA-N 2-[[(e)-6,6-dimethylhept-2-en-4-ynyl]-methylamino]-1-(4-methylphenyl)ethanone Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=O)C1=CC=C(C)C=C1 UGOLIEHVMIQBSZ-SOFGYWHQSA-N 0.000 claims description 4
- QAWLPEAATRFOTH-UHFFFAOYSA-N 4-[3-[(4-tert-butylphenyl)methyl-methylamino]prop-1-enyl]benzoic acid Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC=CC1=CC=C(C(O)=O)C=C1 QAWLPEAATRFOTH-UHFFFAOYSA-N 0.000 claims description 4
- VVQMLYBEYMLMJK-UHFFFAOYSA-N n-[(4-tert-butylphenyl)methyl]-n-methyl-2-(4-piperidin-1-ylphenyl)prop-2-en-1-amine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=C)C(C=C1)=CC=C1N1CCCCC1 VVQMLYBEYMLMJK-UHFFFAOYSA-N 0.000 claims description 4
- CTXQZWNNXGOOQJ-SOFGYWHQSA-N (e)-n-[2-(3,5-difluorophenyl)prop-2-enyl]-n,6,6-trimethylhept-2-en-4-yn-1-amine Chemical compound CC(C)(C)C#C/C=C/CN(C)CC(=C)C1=CC(F)=CC(F)=C1 CTXQZWNNXGOOQJ-SOFGYWHQSA-N 0.000 claims description 3
- HYWCYVDMKYBESX-UHFFFAOYSA-N 4-[2-[(4-tert-butylphenyl)methyl-methylamino]acetyl]benzonitrile Chemical compound C=1C=C(C(C)(C)C)C=CC=1CN(C)CC(=O)C1=CC=C(C#N)C=C1 HYWCYVDMKYBESX-UHFFFAOYSA-N 0.000 claims description 3
- 206010011416 Croup infectious Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 201000010549 croup Diseases 0.000 claims description 3
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- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000013580 millipore water Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical class [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- LBLPBWHJUFIFLB-UHFFFAOYSA-N n-methyl-1-[4-(2-phenylpropan-2-yl)phenyl]methanamine Chemical compound C1=CC(CNC)=CC=C1C(C)(C)C1=CC=CC=C1 LBLPBWHJUFIFLB-UHFFFAOYSA-N 0.000 description 1
- MQRIUFVBEVFILS-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CNC)=CC=CC2=C1 MQRIUFVBEVFILS-UHFFFAOYSA-N 0.000 description 1
- SSNISTUBYRMYDY-UHFFFAOYSA-N n-methyl-1-naphthalen-2-ylmethanamine Chemical compound C1=CC=CC2=CC(CNC)=CC=C21 SSNISTUBYRMYDY-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 201000009862 superficial mycosis Diseases 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 125000006488 t-butyl benzyl group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/52—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
L'invention concerne de nouveaux dérivés d'amine représentés par la formule générale suivante (1), ces dérivés possédant un effet antifongique excellent; l'invention concerne également des sels de ces dérivés. Dans la formule (1) selon l'invention, R?1¿ représente un alkyle en C¿1-5? éventuellement halogéné; R?2¿ représente 4-(1,1-diméthylalkyl) benzyle, 4-(1-méthyl-1-phényléthyl) benzyle ou 1-ou 2-naphthylméthyle ou un hydrocarbure portant 3,3-diméthyl-1-butynyle ou phényle à l'extrémité et possédant 1 à 3 liaisons doubles; R?3¿ représente de l'oxygène ou du méthylène substitué par un alkyle en C¿1-4?; et R?3¿ représente 1- ou 2-naphthyle ou un phényle éventuellement substitué.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22308797 | 1997-08-05 | ||
| JP9-223087 | 1997-08-05 | ||
| JP10-093567 | 1998-04-06 | ||
| JP9356798 | 1998-04-06 | ||
| PCT/JP1998/003487 WO1999007666A1 (fr) | 1997-08-05 | 1998-08-05 | Derives d'amine et leur procede de production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2300273A1 true CA2300273A1 (fr) | 1999-02-18 |
Family
ID=26434899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002300273A Abandoned CA2300273A1 (fr) | 1997-08-05 | 1998-08-05 | Derives d'amine et leur methode de production |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6329399B1 (fr) |
| EP (2) | EP1020426B9 (fr) |
| JP (1) | JP3833471B2 (fr) |
| AT (2) | ATE299489T1 (fr) |
| AU (1) | AU751914C (fr) |
| CA (1) | CA2300273A1 (fr) |
| DE (2) | DE69830850T2 (fr) |
| WO (1) | WO1999007666A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004080945A1 (fr) * | 2003-03-12 | 2004-09-23 | Natco Pharma Limited | Procede de preparation de n-methyl-1-naphthalenemethanamine |
| CN102898314B (zh) * | 2012-11-13 | 2014-09-03 | 山东铂源药业有限公司 | 一种盐酸特比萘芬的制备方法 |
| CN108164423B (zh) * | 2017-12-27 | 2021-07-13 | 福建金山准点制药有限公司 | 一种盐酸萘替芬的制备方法 |
| CN108017544B (zh) * | 2017-12-28 | 2020-05-08 | 山东铂源药业有限公司 | 一种特比萘芬的合成方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1962497C3 (de) * | 1969-12-12 | 1979-09-20 | C.H. Boehringer Sohn, 6507 Ingelheim | Naphthylalkyl- a -hydroxyphenäthyl-amine, ihre Herstellung und diese enthaltende Arzneimittel |
| GB1383186A (en) * | 1972-07-26 | 1975-02-05 | Luso Farmaco Inst | Beta-aminoketone derivatives |
| DE2420618C2 (de) * | 1974-04-27 | 1982-09-16 | C.H. Boehringer Sohn, 6507 Ingelheim | Aminoalkylanilide, Verfahren zu ihrer Herstellung sowie pharmazeutische Zubereitungen, die diese Aminoalkylanilide enthalten |
| DE2809211A1 (de) * | 1978-03-03 | 1979-09-06 | Sandoz Ag | (2-propenyl)-(1-naphthylmethyl) -aminderivate, ihre verwendung und herstellung |
| CH656378A5 (en) * | 1983-05-02 | 1986-06-30 | Sandoz Ag | Allylamine derivatives, process for their preparation, antimycotic agents containing them, and their use |
| JPS6145A (ja) * | 1984-06-09 | 1986-01-06 | Kaken Pharmaceut Co Ltd | N‐(4‐tert‐ブチルベンジル)‐N‐メチル‐1‐ナフチルメチルアミンおよびそれを有効成分とする抗真菌剤 |
| US4871824A (en) | 1987-03-13 | 1989-10-03 | Minnesota Mining And Manufacturing Company | Variably crosslinked polymeric supports |
| DE3720317A1 (de) * | 1987-06-19 | 1988-12-29 | Sandoz Ag | Neue allylaminderivate |
| JP3116364B2 (ja) * | 1989-10-02 | 2000-12-11 | 萬有製薬株式会社 | エンイン誘導体の製造法 |
| AU658134B2 (en) * | 1989-12-28 | 1995-04-06 | Virginia Commonwealth University | Sigma receptor ligands and the use thereof |
| JPH04213308A (ja) | 1990-11-27 | 1992-08-04 | Fuji Photo Film Co Ltd | プロペンアミド誘導体とアニオン性単量体との共重合物およびその用途 |
| JPH0592910A (ja) | 1991-04-03 | 1993-04-16 | Seiwa Kasei:Kk | 化粧品基材 |
| GB9111611D0 (en) * | 1991-05-30 | 1991-07-24 | Sandoz Ltd | Liposomes |
| JPH05124929A (ja) | 1991-10-30 | 1993-05-21 | Pola Chem Ind Inc | 化粧料 |
| EP0588030A3 (fr) | 1992-09-17 | 1995-01-25 | Ibm | Dispositif de maître de microchannel pour convertir en architecture de commutateur. |
| JPH06116287A (ja) | 1992-10-09 | 1994-04-26 | Fuji Photo Film Co Ltd | プロペンアミド誘導体、その重合物およびその用途 |
| JPH08176085A (ja) | 1994-12-27 | 1996-07-09 | Aibaitsu Kk | N−メタクリロイル−アミノ酸エステル、これらの製法およびこれらの重合体 |
| JPH08311004A (ja) | 1995-05-15 | 1996-11-26 | Aibaitsu Kk | N−メタクリロイル−アミノ酸エステル、これらの製法およびこれらの重合体 |
| CA2247675C (fr) * | 1998-09-17 | 2009-05-05 | Pola Chemical Industries, Inc. | Antifongiques |
-
1998
- 1998-08-05 EP EP98936667A patent/EP1020426B9/fr not_active Expired - Lifetime
- 1998-08-05 CA CA002300273A patent/CA2300273A1/fr not_active Abandoned
- 1998-08-05 WO PCT/JP1998/003487 patent/WO1999007666A1/fr not_active Ceased
- 1998-08-05 DE DE69830850T patent/DE69830850T2/de not_active Expired - Fee Related
- 1998-08-05 DE DE69837628T patent/DE69837628T2/de not_active Expired - Fee Related
- 1998-08-05 JP JP2000507203A patent/JP3833471B2/ja not_active Expired - Fee Related
- 1998-08-05 AT AT98936667T patent/ATE299489T1/de not_active IP Right Cessation
- 1998-08-05 US US09/485,309 patent/US6329399B1/en not_active Expired - Fee Related
- 1998-08-05 AT AT05009223T patent/ATE359993T1/de not_active IP Right Cessation
- 1998-08-05 EP EP05009223A patent/EP1561744B1/fr not_active Expired - Lifetime
- 1998-08-05 AU AU85596/98A patent/AU751914C/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE299489T1 (de) | 2005-07-15 |
| EP1020426A1 (fr) | 2000-07-19 |
| EP1561744A2 (fr) | 2005-08-10 |
| AU751914C (en) | 2003-07-24 |
| AU8559698A (en) | 1999-03-01 |
| EP1020426B1 (fr) | 2005-07-13 |
| DE69837628D1 (de) | 2007-05-31 |
| JP3833471B2 (ja) | 2006-10-11 |
| WO1999007666A1 (fr) | 1999-02-18 |
| AU751914B2 (en) | 2002-08-29 |
| DE69830850T2 (de) | 2006-04-20 |
| EP1561744A3 (fr) | 2005-08-24 |
| EP1020426B9 (fr) | 2006-03-22 |
| ATE359993T1 (de) | 2007-05-15 |
| EP1020426A4 (fr) | 2003-02-05 |
| US6329399B1 (en) | 2001-12-11 |
| EP1561744B1 (fr) | 2007-04-18 |
| DE69837628T2 (de) | 2008-01-03 |
| DE69830850D1 (de) | 2005-08-18 |
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| EEER | Examination request | ||
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